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The Stanley Cup had been won and contested since 1893, when the Montreal Hockey Club was the first winner, for winning the 1893 AHAC season. The Cup winner would then have to defend its championship both through league championships and challenge games or series organized by the Stanley Cup trustees.

This changed in 1914 with the inauguration of the first "World Series" of ice hockey,[1] a series between the Stanley Cup and league champion Toronto Hockey Club of the National Hockey Association (NHA) and the Victoria Aristocrats, champions of the Pacific Coast Hockey Association (PCHA). The series was pre-arranged between the two leagues prior to the season after post-season exhibitions held in the previous seasons. The inaugural series was to be held in the city of the NHA champion, and alternate annually thereafter.

After the series got under way, there was some concern that the series would produce an "official" Stanley Cup champion. The Victoria club had not formally applied to the Stanley Cup trustees to challenge for the Cup.[2] A letter arrived from the Stanley Cup trustees on March 17, that the trustees would not let the Stanley Cup travel west, as they did not consider Victoria a proper challenger because they had not formally notified the trustees.[3] However, on March 18, Trustee William Foran stated that it was a misunderstanding. PCHA president Lester Patrick had not filed a challenge, because he had expected Emmett Quinn of the NHA to make all of the arrangements in his role as hockey commissioner, whereas the trustees thought they were being deliberately ignored. In any case, all arrangements had been ironed out and the Victoria challenge was accepted.[4] Any controversy was moot as Toronto successfully defended the Cup by sweeping a best-of-five series in three games.[5] This was the start of the end of the influence of the Stanley Cup trustees on the challengers and series for the Cup. In March 1914, trustee William Foran wrote to NHA president Emmett Quinn that the trustees are "perfectly satisfied to allow the representatives of the three pro leagues (NHA, PCHA and Maritime) to make all arrangements each season as to the series of matches to be played for the Cup."[6]

One year later, the NHA and the PCHA concluded a gentlemen's agreement in which their respective champions would face each other for the Cup. Under the new proposal, the Stanley Cup championship finals alternated between the East and the West each year, with alternating games played according to NHA and PCHA rules.[7] The Cup trustees agreed to this new arrangement, because after the Allan Cup became the highest prize for amateur hockey teams in Canada, the trustees had become dependent on the top two professional leagues to bolster the prominence of the trophy.[8] After the Portland Rosebuds, an American-based team, joined the PCHA in 1914, the trustees issued a statement that the Cup was no longer for the best team in Canada, but now for the best team in the world.[7] Two years later, the Rosebuds became the first American team to play in the Stanley Cup championship finals.[8] In 1917, the Seattle Metropolitans became the first American team to win the Cup.[9] After that season, the NHA dissolved, and the National Hockey League (NHL) took its place.[7]

In 1919, the Spanish influenza epidemic forced the Montreal Canadiens and the Seattle Metropolitans to cancel their series tied at 2–2–1, marking the first time the Stanley Cup was not awarded.[10]

The format for the Stanley Cup championship changed in 1922, with the creation of the Western Canada Hockey League (WCHL). Now three leagues competed for the Cup and this necessitated a semi-final series between two league champions, with the third having a bye directly to the finals.[11] In 1924, the PCHA and the WCHL merged to form the Western Hockey League (WHL) and the championship reverted to a single series.[12] After winning in the 1924–25 season, the Victoria Cougars became the last team outside the NHL to win the Stanley Cup.[13]

The WHL folded in 1926, and most of the players moved to the NHL. This left the NHL as the only league left competing for the Cup. Other leagues and clubs have issued challenges, but from that year forward, no non-NHL team has played for it, leading it to become the de facto championship trophy of the NHL.[12] In 1947, the NHL reached an agreement with trustees P. D. Ross and Cooper Smeaton to grant control of the cup to the NHL, allowing the league itself to reject challenges from other leagues that may have wished to play for the Cup.[14][15] A 2006 Ontario Superior Court case found that the trustees had gone against Lord Stanley's conditions in the 1947 agreement.[16] The NHL has agreed to allow other teams to play for the Cup should the league not be operating, as was the case in the 2004–05 NHL lockout.[15]

The first United States broadcast of the Stanley Cup Finals was in 1962, covered by Chicago station WGN. Network broadcasts started in 1966 on NBC. The Finals have been broadcast by NBC, ABC, CBS, Fox and Hughes broadcast networks and the ESPN, USA, SportsChannel America, Versus, and currently NBC Sports Network cable networks. Several Finals were carried on syndication through the 1970s NHL Network and the 1966 RKO General network. In 2010 and 2011, the games were carried on NBC and Versus and the games will be carried on NBC and NBCSN throughout the 2021 season. This splitting of coverage on cable/broadcast networks originated in 1995 with a partnership of ESPN and Fox.

The championship series began with the 'Worlds Series' played in one city. The series alternated between a rink of the NHA and later the NHL and a rink of the PCHA and later the WCHL/WHL. It was not until the demise of the WHL, that the final series alternated games between the two finalists' home ice.

The series allowed ties until 1928. As the two and later three leagues differed, the series would alternate using each league's rules. The PCHA continued to use seven-man team play, and games would alternate with six and seven-man games.

The first NHL-only final series took place in 1927, between the Boston Bruins and the Ottawa Senators, it was planned to be a best-of-three series, although the series allowed ties. The series ended after four games, when the Senators defeated the Bruins in the fourth game.

The NHL has changed its playoff format several times since 1927, and thus the Cup Finals have not always pitted conference or division playoff champions against each other. In the playoff format used from 1929 to 1938, the two teams with identical division ranking would face each other (i.e. the first place teams played each other, the second place teams play each other, and likewise for the third place teams). The winner of the first place series would automatically advance to the Cup Finals. The winner of the second and third place series would then play each other, with the winner of that series earning the other berth to the Cup Finals.

During the Original Six era, the top four teams made the playoffs, with the first and third place teams battling in one semifinal series, while the second and fourth place teams battled in the other. And from 1975 to 1981, all the playoff teams were seeded regardless of division or conference.

^The NHL officially began referring to the championship series as a singular "Final" circa 2006. However, a significant number of North American media still continue to refer to it as plural "Finals", similar to the NBA Finals.

^Note that one of the above (most points, most goals) is incorrect, as 14 goals are also 14 points. The discrepancy seems to be whether the years prior to 1918 are included in NHL Stanley Cup history.